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Org Lett. 2016 Aug 5;18(15):3614-7. doi: 10.1021/acs.orglett.6b01655. Epub 2016 Jul 13.

n→π* Interactions Are Competitive with Hydrogen Bonds.

Author information

1
Department of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.

Abstract

Because carbonyl groups can participate in both hydrogen bonds and n→π* interactions, these two interactions likely affect one another. Herein, enhancement of an amidic n→π* interaction is shown to reduce the ability of β-keto amides to tautomerize to the enol, indicating decreased hydrogen-bonding capacity of the amide carbonyl group. Thus, an n→π* interaction can have a significant effect on the strength of a hydrogen bond to the same carbonyl group.

PMID:
27409515
PMCID:
PMC5089869
DOI:
10.1021/acs.orglett.6b01655
[Indexed for MEDLINE]
Free PMC Article

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